(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine | 161758-52-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine
• CAS: 161758-52-7
• 化学式: C₂₈H₃₅NO₅
• 分子量: 465.59
• InChiKey: FPHYIOLHIXCJHD-QAYXJGBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine 在 二乙基异丙基胺 、 氰基磷酸二乙酯 、 boron trifluoride diacetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1(S)-((5(S)-((tert-Butoxycarbonyl)amino)-4(S)-hydroxy-6-phenyl-2(S)-(2-phenylethenyl)esanoyl)amino)-2(R)-hydroxyindan
  参考文献：
  名称：

  Stereoselective "Ene" Reaction of Allylsilanes with Amino Aldehydes. An Application to the Synthesis of Potential HIV-1 Protease Inhibitors

  摘要：

  2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-alpha-amino aldehydes in the presence of BF3.OEt(2) to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)-3-(trimethylsilyl)-1-propene (5) exhibits a higher stereoselectivity with respect to other analogous allylsilanes. We hypothesize that this selectivity is due to an ''ene'' reaction followed by desilylation in the reaction medium (BF3.OEt(2), CHCl3). This reaction shows applicability to the synthesis of potential HIV-1 protease inhibitors. The preparation of compound 3, which has a structure related to the potent inhibitor L-682,679, is described.

  DOI：

  10.1021/jo00093a006
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 dimethyl sulfide borane 、 四丁基氟化铵 、 双氧水 、 四氯化锡 、 碳酸氢钠 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 甲苯 、 叔丁醇 为溶剂， 反应 82.66h， 生成 (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine
  参考文献：
  名称：

  Stereoselective "Ene" Reaction of Allylsilanes with Amino Aldehydes. An Application to the Synthesis of Potential HIV-1 Protease Inhibitors

  摘要：

  2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-alpha-amino aldehydes in the presence of BF3.OEt(2) to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)-3-(trimethylsilyl)-1-propene (5) exhibits a higher stereoselectivity with respect to other analogous allylsilanes. We hypothesize that this selectivity is due to an ''ene'' reaction followed by desilylation in the reaction medium (BF3.OEt(2), CHCl3). This reaction shows applicability to the synthesis of potential HIV-1 protease inhibitors. The preparation of compound 3, which has a structure related to the potent inhibitor L-682,679, is described.

  DOI：

  10.1021/jo00093a006

文献信息

• Stereoselective "Ene" Reaction of Allylsilanes with Amino Aldehydes. An Application to the Synthesis of Potential HIV-1 Protease Inhibitors
  作者：Fabiana D'Aniello、Andre Mann、Duccio Mattii、Maurizio Taddei

  DOI：10.1021/jo00093a006

  日期：1994.7

  2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-alpha-amino aldehydes in the presence of BF3.OEt(2) to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)-3-(trimethylsilyl)-1-propene (5) exhibits a higher stereoselectivity with respect to other analogous allylsilanes. We hypothesize that this selectivity is due to an ''ene'' reaction followed by desilylation in the reaction medium (BF3.OEt(2), CHCl3). This reaction shows applicability to the synthesis of potential HIV-1 protease inhibitors. The preparation of compound 3, which has a structure related to the potent inhibitor L-682,679, is described.